1899 U.S. National Championships – Men's singles
# 1899 U.S. National Championships – Men's singles

Defending champion Malcolm Whitman defeated Jahial Parmly Paret in the challenge round, 6–1, 6–2, 3–6, 7–5 to win the men's singles tennis title at the 1899 U.S. National Championships.

## Draw

### Challenge round

| Challenge round | Challenge round | Challenge round | Challenge round | Challenge round | Challenge round | Challenge round |
| - | - | - | - | - | - | - |
| MD Whitman | MD Whitman | 6 | 6 | 3 | 7 | |
| J Parmly Paret | J Parmly Paret | 1 | 2 | 6 | 5 | |

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final | Final | Final | Final |
| - | - | - | - | - | - | - | - | - | - | - | - |
| LE Ware | LE Ware | 5 | 2 | 4 | | | | | | | |
| J Parmly Paret | J Parmly Paret | 7 | 6 | 6 | | | | | | | |
| J Parmly Paret | J Parmly Paret | 7 | 6 | 6 | J Parmly Paret | J Parmly Paret | 7 | 8 | 6 | 2 | 6 |
| | | | | | D Davis | D Davis | 5 | 10 | 3 | 6 | 4 |
| D Davis | D Davis | 6 | 6 | 8 | D Davis | D Davis | 5 | 10 | 3 | 6 | 4 |
| K Collins | K Collins | 4 | 1 | 6 | | | | | | | |

### Earlier rounds

**Section 1**

| Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| J Appleton Allen | J Appleton Allen | | | | | | | | | | | | | | | | | |
| NH Mundy | NH Mundy | w/ | o | | | | | | | | | | | | | | | |
| | | | | | | NH Mundy | NH Mundy | 6 | 8 | 2 | 0 | | | | | | | |
| | | | | | | H Ward | H Ward | 4 | 10 | 6 | 6 | | | | | | | |
| H Ward | H Ward | 6 | 6 | 4 | 6 | | | | | | | | | | | | | |
| CR Budlong | CR Budlong | 4 | 4 | 6 | 2 | | | | | | | | | | | | | |
| | | | | | | | | | | | | H Ward | H Ward | 6 | 4 | 11 | 2 | 4 |
| | | | | | | | | | | | | LE Ware | LE Ware | 3 | 6 | 9 | 6 | 6 |
| EA Freshman | EA Freshman | 2 | 4 | 3 | | | | | | | | | | | | | | |
| A Codman | A Codman | 6 | 6 | 6 | | | | | | | | | | | | | | |
| | | | | | | A Codman | A Codman | 7 | 3 | 3 | | | | | | | | |
| | | | | | | LE Ware | LE Ware | 9 | 6 | 6 | | | | | | | | |
| N McLeod | N McLeod | | | | | | | | | | | | | | | | | |
| LE Ware | LE Ware | w/ | o | | | | | | | | | | | | | | | |

**Section 2**

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| | | | | | M Chace | M Chace | 6 | 8 | 0 | 3 | | | | | | | | | | | | | | |
| | | | | | J Parmly Paret | J Parmly Paret | 3 | 10 | 6 | 6 | | | | | | | | | | | | | | |
| | | | | | | | | | | | J Parmly Paret | J Parmly Paret | 6 | 6 | 6 | | | | | | | | | |
| | | | | | | | | | | | H Avery | H Avery | 2 | 3 | 3 | | | | | | | | | |
| | | | | | W Larned | W Larned | | | | | | | | | | | | | | | | | | |
| | | | | | H Avery | H Avery | w/ | o | | | | | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | J Parmly Paret | J Parmly Paret | 3 | 6 | 4 | 6 | 6 |
| | | | | | | | | | | | | | | | | | | B Huntington | B Huntington | 6 | 3 | 6 | 4 | 0 |
| | | | | | HW Stiness | HW Stiness | | | | | | | | | | | | | | | | | | |
| R Stevens | R Stevens | w/ | o | | R Stevens | R Stevens | w/ | o | | | | | | | | | | | | | | | | |
| D Miller | D Miller | | | | | | | | | | R Stevens | R Stevens | 6 | 6 | 3 | 3 | 1 | | | | | | | |
| RD Little | RD Little | w/ | o | | | | | | | | B Huntington | B Huntington | 2 | 3 | 6 | 6 | 6 | | | | | | | |
| F Huntington | F Huntington | | | | RD Little | RD Little | 4 | 6 | 4 | | | | | | | | | | | | | | | |
| B Huntington | B Huntington | 6 | 8 | 6 | B Huntington | B Huntington | 6 | 8 | 6 | | | | | | | | | | | | | | | |
| R McKittrick | R McKittrick | 2 | 6 | 4 | | | | | | | | | | | | | | | | | | | | |

**Section 3**

| First round | First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| WS Bond | WS Bond | 6 | 4 | 6 | 6 | | | | | | | | | | | | | | | | | | |
| W Clothier | W Clothier | 3 | 6 | 4 | 4 | WS Bond | WS Bond | 6 | 6 | 6 | | | | | | | | | | | | | |
| JS Bridges | JS Bridges | w/ | o | | | JS Bridges | JS Bridges | 1 | 2 | 0 | | | | | | | | | | | | | |
| P Whitney | P Whitney | | | | | | | | | | WS Bond | WS Bond | 4 | 6 | 7 | 4 | 6 | | | | | | |
| BC Wright | BC Wright | w/ | o | | | | | | | | BC Wright | BC Wright | 6 | 4 | 5 | 6 | 3 | | | | | | |
| G Sheldon | G Sheldon | | | | | BC Wright | BC Wright | 6 | 6 | 6 | | | | | | | | | | | | | |
| | | | | | | LJ Grant | LJ Grant | 2 | 2 | 1 | | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | WS Bond | WS Bond | 4 | 4 | 6 | 4 |
| | | | | | | | | | | | | | | | | | | D Davis | D Davis | 6 | 6 | 1 | 6 |
| | | | | | | CN Beard | CN Beard | 6 | 6 | 8 | | | | | | | | | | | | | |
| | | | | | | DS Ricker | DS Ricker | 2 | 2 | 6 | | | | | | | | | | | | | |
| | | | | | | | | | | | CN Beard | CN Beard | 0 | 1 | | | | | | | | | |
| | | | | | | | | | | | D Davis | D Davis | 6 | 6 | | | | | | | | | |
| | | | | | | D Davis | D Davis | 6 | 6 | 6 | | | | | | | | | | | | | |
| | | | | | | HG Whitehead | HG Whitehead | 2 | 4 | 0 | | | | | | | | | | | | | |

**Section 4**

| Second round | Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| GL Wrenn | GL Wrenn | 5 | 8 | 7 | 6 | | | | | | | | | | | | | |
| EP Fischer | EP Fischer | 7 | 6 | 5 | 2 | | | | | | | | | | | | | |
| | | | | | | | GL Wrenn | GL Wrenn | 6 | 6 | 6 | | | | | | | |
| | | | | | | | JS Taylor | JS Taylor | 2 | 3 | 3 | | | | | | | |
| JS Taylor | JS Taylor | 5 | 3 | 6 | 3 | 6 | | | | | | | | | | | | |
| JK Willing | JK Willing | 7 | 6 | 3 | 6 | 2 | | | | | | | | | | | | |
| | | | | | | | | | | | | GL Wrenn | GL Wrenn | 6 | 6 | 6 | 4 | 3 |
| | | | | | | | | | | | | K Collins | K Collins | 8 | 4 | 4 | 6 | 6 |
| T Sturgis | T Sturgis | 3 | 1 | 1 | | | | | | | | | | | | | | |
| K Collins | K Collins | 6 | 6 | 6 | | | | | | | | | | | | | | |
| | | | | | | | K Collins | K Collins | 6 | 6 | 6 | | | | | | | |
| | | | | | | | WC Grant | WC Grant | 1 | 1 | 2 | | | | | | | |
| WC Grant | WC Grant | w/ | o | | | | | | | | | | | | | | | |
| E Stille | E Stille | | | | | | | | | | | | | | | | | |
